Super-cheeks and super-lips won't flap and wave as much as a mortal human's, and super-eyes have no need to squint against the wind. How would you deal with the instinctive tendency to squint for eye protection, against actual wind like that?
However, super-hair might get blown back more or less exactly like a mortal's would, and the forehead curl might really disappear, from being blown back, until he slows down or lands.
I should amend my remarks about squinting to say that he shouldn't be squinting as much
as a mortal. What I meant was, at speeds up to terminal velocity of a skydiver, Superman should have no need to squint.
I don't expect the cape to flap at all at supersonic speeds, so I implicitly assumed a skydiver would only be used to film scenes when he was going, say, only a few hundred mph, in any case.